Bovine Metabolome Database: Showing metabocard for Leucinic acid (BMDB0000665)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:34:34 UTC

Update Date

2020-04-22 15:04:41 UTC

BMDB ID

BMDB0000665

Secondary Accession Numbers

BMDB00665

Metabolite Identification

Common Name

Leucinic acid

Description

Leucinic acid, also known as leucate, belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group. Based on a literature review a significant number of articles have been published on Leucinic acid.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Hydroxyisocaproic acid	ChEBI
2-Hydroxyisohexanoic acid	ChEBI
alpha-Hydroxyisocaproic acid	ChEBI
Leucic acid	ChEBI
2-Hydroxyisocaproate	Generator
2-Hydroxyisohexanoate	Generator
a-Hydroxyisocaproate	Generator
a-Hydroxyisocaproic acid	Generator
alpha-Hydroxyisocaproate	Generator
Α-hydroxyisocaproate	Generator
Α-hydroxyisocaproic acid	Generator
Leucate	Generator
Leucinate	Generator
alpha-Hydroxyisocaproic acid, (R)-isomer	HMDB
alpha-Hydroxyisocaproic acid, calcium (2:1) salt, (S)-isomer	HMDB
alpha-Hydroxyisocaproic acid, monosodium salt	HMDB
alpha-Hydroxyisocaproic acid, (S)-isomer	HMDB
2-Hydroxy-4-methyl-valerate	HMDB
2-Hydroxy-4-methyl-valeric acid	HMDB
2-Hydroxy-4-methylpentanoate	HMDB
2-Hydroxy-4-methylpentanoic acid	HMDB
2-Hydroxy-4-methylvalerate	HMDB
2-Hydroxy-4-methylvaleric acid	HMDB
a-Hydroxy-iso-caproate	HMDB
a-Hydroxy-iso-caproic acid	HMDB
alpha-Hydroxy-iso-caproate	HMDB
alpha-Hydroxy-iso-caproic acid	HMDB
DL-2-Hydroxy-4-methylpentanoate	HMDB
DL-2-Hydroxy-4-methylpentanoic acid	HMDB
DL-2-Hydroxyisocaproate	HMDB
DL-2-Hydroxyisocaproic acid	HMDB
DL-a-Hydroxyisocaproate	HMDB
DL-a-Hydroxyisocaproic acid	HMDB
DL-alpha-Hydroxyisocaproate	HMDB
DL-alpha-Hydroxyisocaproic acid	HMDB
DL-Leucate	HMDB
DL-Leucic acid	HMDB
Leucinic acid	ChEBI

Chemical Formula

C₆H₁₂O₃

Average Molecular Weight

132.1577

Monoisotopic Molecular Weight

132.07864425

IUPAC Name

2-hydroxy-4-methylpentanoic acid

Traditional Name

leucate

CAS Registry Number

498-36-2

SMILES

CC(C)CC(O)C(O)=O

InChI Identifier

InChI=1S/C6H12O3/c1-4(2)3-5(7)6(8)9/h4-5,7H,3H2,1-2H3,(H,8,9)

InChI Key

LVRFTAZAXQPQHI-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Hydroxy fatty acids

Alternative Parents

Substituents

Branched fatty acid
Hydroxy fatty acid
Methyl-branched fatty acid
Alpha-hydroxy acid
Hydroxy acid
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Carbonyl group
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

2-hydroxy fatty acid (CHEBI:59783 )
branched-chain fatty acid (CHEBI:59783 )
Hydroxy fatty acids (LMFA01050381 )

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Adiposome
Cell membrane
Cytoplasm
Membrane

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	886 mg/mL	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.5	ALOGPS
logP	0.78	ChemAxon
logS	-0.03	ALOGPS
pKa (Strongest Acidic)	4.26	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	32.51 m³·mol⁻¹	ChemAxon
Polarizability	13.65 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-0883a44db52a6c25fe99	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-02gc-9440000000-7fffd162011678b17f4a	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-014r-9000000000-5e0d546d1d0e6bb8c48c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-014i-9100000000-ed29dea8a5c4015ec5f9	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0a4i-8900000000-44e1b9618ac09f8f20b8	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-001r-7900000000-7ab0c9dc80e61fa580c9	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-001r-7900000000-7ab0c9dc80e61fa580c9	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-000i-9100000000-b13176bdf03a9a3860aa	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0006-9000000000-702157a92667487bd5f6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00lr-7900000000-d13b28975eefc974bbca	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ap0-9200000000-aaa07e44b97e9617d7f1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-931176b5fcc7e8bde29c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-4900000000-c818e3e6474333b25326	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-053i-9200000000-bd611de2f2748fe8a7fa	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ap0-9000000000-4e37e159ea3117d8a516	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0019-9700000000-a7d0b1ce1c211b31bc0d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00kr-9100000000-504826b66e199a65ef09	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014l-9000000000-ccecb4a470c359949fec	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-9000000000-3019a9d0620e7da01963	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kf-9000000000-e587d44396e53f2409fa	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-457ece1d510dad645c89	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Adiposome
Cell membrane
Cytoplasm
Membrane

Biospecimen Locations

Not Available

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0000665

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022171

KNApSAcK ID

Not Available

Chemspider ID

83753

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5635

PubChem Compound

92779

PDB ID

Not Available

ChEBI ID

59783

References

Synthesis Reference

Camien, Merill N.; Fowler, Audree V.; Dunn, Max S. Production of a-hydroxy fatty acids by two strains of Lactobacillus casei. Archives of Biochemistry and Biophysics (1959), 83 408-18.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Leucinic acid (BMDB0000665)

Structure for BMDB0000665 (Leucinic acid)